Tough Questions: What’s the Worst Date You’ve Ever Been On?


Every week we ask everyone who hangs out around here to answer a tough question. This week:

What’s the worst date you’ve ever been on?

Rules are simple: so, like, what do you do for fun? Dating is extremely stressful, because it requires exactly the right blend of being honest about yourself and shielding a near-stranger from the horrible truth of who you are. Dating is exciting because it’s full of possibility, but one of those possibilities is that it will go really, really badly. What’s your worst experience?

Alex Russell

There have been a few, but nothing will ever dethrone the very first one. I was 13 and painfully shy, but I met a girl at a friend’s party and we hit it off. I don’t know how much one can “hit it off” at 13, but it at least went well enough that she wanted to see me again. She invited me to her friend’s party the next week and told me it was a “fancy dress-up party.” I showed up in loafers and a suit coat, and everyone else was ready for what was clearly a swimming event. I never figured out if she made an honest mistake or if she was just evil. As some kind of gesture to show I was a good sport, I jumped in and swam in my 13-year-old “nice clothes” anyway. An auspicious start.

Jonathan May

I’ve been on a ton of horrible dates. But one time really takes the cake. I was seeing this guy who wasn’t really my type, but he was really into me, so I thought, “What the heck? Okay.” He wanted to take me to a movie, which is my least favorite kind of date because you don’t actually talk to the other person at all. Well, I wanted to see Tree of Life, which (trust me) is not a date film. Halfway through the film, as Jessica Chastain’s character hovers mid-air, I started to cry because I was struck by the movie’s poetic beauty. It was at this exact moment that he tried to hold my hand. I can’t describe how little I wanted anyone to touch me right then and there in the dark theater, with a billion emotions roiling within me. That was the camel’s straw. Afterward, I begged off going for dinner due to a headache, which I didn’t even have to fabricate at that point. Ugh, the worst.

Brent Hopkins

The worst date I went on was with a Korean lady who started off by informing me that she always wanted to go out with a black dude but that I wasn’t that black in skin color and actions. I guess she saw me as training wheels to the “real” thing or something. I tried to explain that his was not something that was okay to say, which led me down this road of trying to figure out what type of backhanded offensive things I could say to her to get her to understand. So, yeah, I had a date that was entirely based on racism and stereotyping and it was, the suck, as they say.

Andrew Findlay

I met my wife when I was 18, so the only bad dates I’ve ever been on were bad teenager dates, where neither of you know what to do or what you want, and both of you are just super awkward for basically all the time you spend together. It was ten years ago though man, so I don’t know.

Gardner Mounce

The weirdest date I’ve ever been on happened when I was in 8th grade and was dating a girl I’ll call C. C and I were at her house one night watching a movie. C decided it’d be fun to get in her hot tub out back. We did. After a little while, her mom, who we both thought was upstairs sleeping, came out with a camera and asked if she could take a picture of us kissing. Ladies and gentlemen, I have never felt more uncomfortable. I wish I could say I declined, but I didn’t. I rest uneasy knowing that her mom probably still looks at that thing.

Colton Royle

I once went on a date with a woman who advocated for a fascist educational system. “Maybe some people with lower IQ’s should be taught what to think.” We report. You decide.

Dating Naked: VH1’s New Reality Dating Show Mixes Dating and… Naked People

Dating Naked

Jonathan May

I watched the premiere of VH1’s Dating Naked over the weekend, and it was about as floppy as many of the blurred out genitals during the course of the dates. The premise is achingly simple: one girl and one guy meet and go on a naked date, and then a proper date with clothes. The next day, each go on a date with a different person (also naked), ending with each date being brought back to the house for subtle inspection by all parties. This happens one more time. So on the last night, there are three girls and three guys, usually all naked, in the pool. The spin isn’t terribly original, nor are any of the jokes made about nudity during the surprisingly endless 30 minutes.

The truly unfortunate part is that, in this episode in any case, the initial woman falls for the initial man much harder than he for her; I can’t tell if the show’s production was adept at finding the right obsessively emotional girl, or if they just picked one of many. The show makes the tacit statement that women are more emotionally needy than men, and through careful casting and a splash of alcohol, it achieves its effect. Men are cast as untamable lotharios, and women as needy vixens. What’s new?

But the initial pair doesn’t enter quite so jaded. Each speaks to the camera of looking for The One and finding someone who is genuine, but as soon as gorgeous naked bodies come into play, a lot of the emotional criteria fall by the way. By the end of the episode, the initial Adam and Eve pair must each pick one person whom they’d like to date later; they are free to pick each other as well. I won’t ruin the ending, but needless to say, the production of the show rests soundly on the scant bits of blur on otherwise completely naked, mostly attractive, Americans.

Like all reality dating shows, this focuses on minor bitchy dramas and sexual farces to keep it moving; it’s unclear how much is scripted and how much might actually be sincere, but it feels like sincerity is beside the point in a show where all the contestants are nude. It’s safe to say Dating Naked isn’t breaking any new ground, but it was still more interesting than any other dating show I’ve seen on television in the past few years. Though I doubt the show will create any kind of fandom, I’ll probably still be tuning in next week.

Jonathan May watches too much television, but he’s just playing catch-up from a childhood spent in Zimbabwe. You can read his poetry at, follow him on Twitter at @jonowenmay, or email him at